Synlett,
Journal Year:
2022,
Volume and Issue:
34(04), P. 293 - 300
Published: Nov. 20, 2022
Abstract
The
reassembly
of
unsaturated
C–C
bonds
has
attracted
widespread
attention
from
synthetic
chemists
due
to
its
advantages
unique
reactivity,
easy
handling,
and
high
atom
step
economies.
We
recently
explored
a
cutting/insertion
cascade
as
means
introducing
new
C1
source
constructing
functionalized
1,4-keto
aldehyde
2H-furan
derivatives
through
cyclopropanation
enamines
with
various
carbene
precursors
subsequent
ring-opening
reactions
in
situ.
Aminocyclopropanes
are
believed
be
involved
key
intermediates
these
transformations.
This
Synpacts
article
outlines
our
recent
contributions
this
increasingly
important
research
area.
1
Introduction
2
Cleavage
Enamine
C=C
Double
Bonds
Hydrolysis
1,4-Keto
Aldehydes
3
Cyclization
2H-Furans
4
Ynone/Ynoate
C≡C
Triple
5
Conclusion
Organic Letters,
Journal Year:
2023,
Volume and Issue:
25(16), P. 2868 - 2872
Published: April 19, 2023
Difluorocarbene-triggered
[1+5]
annulation
is
developed
to
access
1,1-difluoro-1,9a-dihydropyrido[2,1-c][1,4]thiazine-3,4-dicarboxylate
derivatives
in
satisfactory
good
yields
via
the
direct
reaction
of
potassium
bromodifluoroacetate
and
pyridinium
1,4-zwitterionic
thiolates
under
heating.
Pyridinium
first
nucleophilically
attack
difluorocarbene
generated
from
followed
by
an
intramolecular
nucleophilic
addition
pyridiniums.
This
method
provides
expeditious
route
introduce
difluoromethyl
group
into
1,9a-dihydropyrido[2,1-c][1,4]thiazine
ring,
even
modify
drug
molecules.
Organic Chemistry Frontiers,
Journal Year:
2024,
Volume and Issue:
11(15), P. 4214 - 4218
Published: Jan. 1, 2024
A
[3
+
1
1]
cascade
annulation
reaction
for
the
divergent
construction
of
trisubstituted
indolizines
using
sulfoxonium
ylides,
BrCF
2
CO
Me
and
pyridinium
salts
as
readily
available
substrates
has
been
developed.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: Feb. 6, 2025
A
novel
approach
to
the
synthesis
of
β-CF3
β-aminoenones
by
organic
amine
base-catalyzed
reaction
CF3-iminopropargylic
alcohols
with
carboxylic
acids
is
reported.
The
advantages
protocol
are
ease
operation,
available
starting
materials,
and
simple
tertiary
catalysts.
The Journal of Organic Chemistry,
Journal Year:
2025,
Volume and Issue:
unknown
Published: May 8, 2025
Computational
studies
on
all
proposed
possible
mechanisms
of
the
annulations
difluorocarbene
and
enaminones
were
carried
out,
providing
comprehensive
mechanistic
insights
into
annulations.
The
results
suggest
that
asynchronous
concerted
[4
+
1]
cycloaddition
is
more
favorable
for
annulation
enaminones,
leading
to
2,2-difluoro-2,3-dihydrofuran-3-amine
derivatives
hardly
3,3-difluoro-2,3-dihydrofuran-2-amine
derivatives,
which
even
documented
be
obtained
should
minor
products.
calculation
further
verified
experimentally.
current
provide
a
thorough
understanding
correct
an
unreasonable
reported
result.
Organic & Biomolecular Chemistry,
Journal Year:
2024,
Volume and Issue:
22(20), P. 4067 - 4071
Published: Jan. 1, 2024
Rapid
assembly
of
quinoxalines
in
a
single
step
from
readily
available
precursors
has
been
recognized
as
an
ideal
platform
terms
efficiency
and
operation.
Herein,
we
report
BPO-promoted
metal-free
approach
to
2-acyl
enaminones
The Journal of Organic Chemistry,
Journal Year:
2024,
Volume and Issue:
89(13), P. 9496 - 9501
Published: June 18, 2024
Herein,
an
unprecedented
[4
+
2]
cycloaddition
of
enaminone
with
1,3,5-triazinane
has
been
developed.
The
representative
semihydrogenated
aromatic
heterocycle
1,2,3,4-tetrahydropyrimidines
have
synthesized
a
broad
substrate
scope,
demonstrating
potential
antitumor
activity.
This
approach
smoothly
conducted
under
additive-free
and
environmentally
friendly
conditions
that
are
compatible
various
functional
groups.
Furthermore,
the
condition
optimization
process
reveals
tetrahydropyrimidine
product
is
regulated
via
reaction
temperature.
Organic Letters,
Journal Year:
2024,
Volume and Issue:
26(18), P. 3744 - 3749
Published: April 30, 2024
2-Fluorobenzofurans
are
the
backbone
structures
of
many
drug
molecules
and
have
potential
therapeutic
bioactivities.
Despite
applications
in
medicinal
chemistry,
practical
efficient
synthetic
methods
for
construction
2-fluorobenzofuran
very
limited.
Herein,
we
report
an
general
method
2-fluorobenzofurans.
Contrary
to
previous
functionalizations
existing
benzofuran,
our
strategy
directly
constructs
benzofuran
scaffolds
alongside
incorporation
fluorine
atom
on
C2
position
a
formal
[4
+
1]
cyclization
from
readily
accessible
Organic Process Research & Development,
Journal Year:
2024,
Volume and Issue:
28(7), P. 2765 - 2769
Published: May 7, 2024
An
efficient,
scalable
synthesis
of
functionalized
5-fluoropyrrolo[2,1-f][1,2,4]triazines
was
developed
from
readily
available
starting
materials.
The
is
highlighted
by
a
safe,
Cu
mediated
difluoroacetate
addition
to
vinyl
TMS,
selective
formylation
3-fluoropyrrole,
and
sequential
imine
formation
followed
cyclization
the
triazine
core.
Addition
other
electrophiles
3-fluoropyrrole
also
shown
be
equally
selective.
